Reaction #155412

Reaction equation

Lithium aluminium hydride

3-chloro-4-hydroxyphenyl thiocyanate

→

2-chloro-4-mercaptophenol

Yield 100.0%

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   TemperatureThe mixture was cooled to 5° C.
2. 2
   Otherquenched with a 1:1 mixture of tetrahydrofuran
3. 3
   workup.ADDITION1N hydrochloric acid solution in water (30 mL) was then added
4. 4
   Extractionthe mixture extracted with ethyl acetate (2-fold 70 mL)
5. 5
   DryingThe combined organic layers were dried (sodium sulphate)
6. 6
   Concentrationconcentrated in vacuo
7. 7
   Otheraffording a colourless crystalline solid, 100% yield, 3.60 g

Procedure

Lithium aluminium hydride (as a 1M solution in tetrahydrofuran, 71.0 ml, 71.0 mmol) was added dropwise to an ice cold solution of 3-chloro-4-hydroxyphenyl thiocyanate (4.20 g, 22.6 mmol) in tetrahydrofuran (100 mL) under nitrogen. The reaction mixture was stirred and allowed to warm to room temperature over 5 hours. The mixture was cooled to 5° C. and quenched with a 1:1 mixture of tetrahydrofuran:water until no more gas evolution was seen. 1N hydrochloric acid solution in water (30 mL) was then added, and the mixture extracted with ethyl acetate (2-fold 70 mL). The combined organic layers were dried (sodium sulphate) and concentrated in vacuo affording a colourless crystalline solid, 100% yield, 3.60 g.

Source